INTRAMOLECULAR ADDITION OF CARBON-CENTERED TINTHIOIMIDOYL RADICALS TO CARBON CARBON DOUBLE-BONDS - SYNTHESIS OF GAMMA-THIOLACTAMS AND DELTA-THIOLACTAMS

被引:55
作者
BACHI, MD
DENENMARK, D
机构
[1] Department of Organic Chemistry, The Weizmann Institute of Science
关键词
D O I
10.1021/jo00298a008
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
: (Tri-rc-butyltin)thioimidoyl radicals of type 6, which were efficiently generated by treatment of alk-3-enyl-and alk-4-enylisothiocyanates with tri-n-butyltin hydride and AIBN, underwent exo cyclization to give, after hydrolysis, the corresponding 7- or 5-thiolactams in good to excellent yields. © 1990, American Chemical Society. All rights reserved.
引用
收藏
页码:3442 / 3444
页数:3
相关论文
共 30 条
[1]  
BACHI MD, 1989, HETEROCYCLES, V28, P583
[2]   CYCLIZATIONS OF ENE RADICALS - IMIDOYL RADICALS AS INTERMEDIATES IN THE SYNTHESIS OF HETEROCYCLIC-COMPOUNDS [J].
BACHI, MD ;
DENENMARK, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (05) :1886-1888
[3]  
BACHI MD, 1989, HETEROCYCLES, V28, P579
[4]   SYNTHESIS OF ALPHA-ALKYLIDENE-GAMMA-LACTONES BY INTRAMOLECULAR ADDITION OF ALKOXYCARBONYL FREE-RADICALS TO ACETYLENES [J].
BACHI, MD ;
BOSCH, E .
TETRAHEDRON LETTERS, 1986, 27 (05) :641-644
[5]   REACTIONS OF RELEVANCE TO THE CHEMISTRY OF AMINOGLYCOSIDE ANTIBIOTICS .14. A USEFUL RADICAL-DEAMINATION REACTION [J].
BARTON, DHR ;
BRINGMANN, G ;
LAMOTTE, G ;
MOTHERWELL, WB ;
MOTHERWELL, RSH ;
PORTER, AEA .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (12) :2657-2664
[6]  
BARTON DHR, 1980, SYNTHESIS-STUTTGART, P68
[7]   STEREOSELECTIVITY OF RING-CLOSURE OF SUBSTITUTED HEX-5-ENYL RADICALS [J].
BECKWITH, ALJ ;
LAWRENCE, T ;
SERELIS, AK .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1980, (11) :484-485
[8]   REGIO-SELECTIVITY AND STEREO-SELECTIVITY OF ALKENYL RADICAL RING-CLOSURE - A THEORETICAL-STUDY [J].
BECKWITH, ALJ ;
SCHIESSER, CH .
TETRAHEDRON, 1985, 41 (19) :3925-3941
[9]   REGIO-SELECTIVITY AND STEREO-SELECTIVITY IN RADICAL REACTIONS [J].
BECKWITH, ALJ .
TETRAHEDRON, 1981, 37 (18) :3073-3100
[10]  
BOGER DL, 1988, J ORG CHEM, V53, P377